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tert-Butanol → [6-(5-tert-Butoxycarbonylamino-thiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

HRID 1798287
ノート
印刷プレビュー

反応式

HRID 1798287 の反応式
[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[S:20][C:21](C(O)=O)=[CH:22][N:23]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)=[O:5])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.C([N:46]([CH2:49]C)CC)C.[CH3:51][C:52]([OH:55])([CH3:54])[CH3:53]>>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[S:20][C:21]([NH:46][C:49]([O:55][C:52]([CH3:54])([CH3:53])[CH3:51])=[O:34])=[CH:22][N:23]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 582928242-(3-Ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-5-carboxylic acid

生成物 1

HCID 58292561[6-(5-tert-Butoxycarbonylamino-thiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester
収率 45%

反応条件

温度
95 °C

実験手順

To a solution of 2-(3-ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-5-carboxylic acid (500 mg, 1.33 mmol) in tBuOH (10 mL) was added diphenylphosphoryl azide (0.35 mL, 1.61 mmol) and triethylamine (0.41 mL, 2.95 mmol), the reaction mixture was heated to 95° C. for 1 h. The solvent was removed under vacuum and the residue was extracted with ethyl acetate. The organic portion was washed with water and brine, and dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, DCM/MeOH=20:1) affording the title compound (270 mg, 45%) as a white solid. 1H NMR (CDCl3) δ 7.35 (s, 1H), 7.10 (s, 1H), 6.79 (s, 1H), 5.61 (dd, 1H), 4.17 (q, 2H), 3.02 (dd, 1H), 2.37 (m, 1H), 2.30 (s, 3H), 1.48 (s, 9H), 1.23 (t, 3H).

後処理

  1. customThe solvent was removed under vacuum
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic portion was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica, DCM/MeOH=20:1)

出典と根拠

ORDレコード
ord-4e60926bc7d4432da1bd4db90c91d0cb
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08343944B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート